Paid an LLC insurance premium with my personal card. 6,800 to unwind.
Checkbook IRA structure, single member LLC owned by the IRA, me as non-compensated manager. Held two performing seconds and a small unleveraged participation in a rented duplex through the LLC. Ran clean for about two years.
What happened: the LLC operating account got frozen for four days over a fraud flag on a wire I'd sent. The duplex hazard policy lapse notice hit during those four days, 412 dollars, cancellation in 48 hours. I paid it on my personal card intending to reimburse the LLC when the account opened. Also approved a 190 dollar plumbing invoice the same week off the same card.
I reimbursed myself eleven days later out of the LLC and wrote a memo line. Thought that was the end of it.
My CPA did not think that was the end of it. Advancing personal funds to an IRA-owned entity looks like an extension of credit between me and my plan, and the fact that it was small and repaid doesn't obviously fix it. The exposure isn't a 602 dollar problem. If it's treated as a prohibited transaction the account can be treated as ceasing to be an IRA as of the first day of that tax year, and the whole balance becomes a taxable event. Six figures, over one insurance bill.
Spent about 6,800 on a tax attorney and additional CPA hours getting an opinion, a corrected paper trail, and a decision on how to report. I'm not going to describe the resolution because it's specific to my facts and my counsel.
What I'd do differently: keep 90 days of every foreseeable expense as cash inside the LLC account, and set up a second LLC account at a different institution so a freeze at one doesn't create a moment where paying out of pocket feels like the only option. And a written standing instruction to the property manager that no IRA-owned asset expense ever gets paid by me, even if the policy cancels. Let it cancel and rebind. That's cheaper.